I can’t pinpoint the exact moment when I started setting up a yearly plan for myself. It has been a while, at least since 2006. The system that I use has changed over the years with the latest iteration looking something like this:

Identify the value areas that are important to me or need work (e.g. finances, family, career)

A set of goals are then created that fit one or more of these value areas

A goal is broken up into actionable and measurable tasks (not an easy thing to do at times)

The tasks are then scheduled in a calendar, with various reminder points set along the way

And then I do weekly and monthly check-ins to see where I stand in relation of achieving my goals. I try to answer questions such as what are my active tasks, what is working well, what have I failed at recently, what needs to be corrected, and what is next.

And off it goes. I try to knock the tasks out while expecting setbacks and failures along the way. Most important though is to continue to make progress, experiment, and have fun.

Let me give you an example. This is a story of how I used this system to sell a small piece of property that I had been procrastinating about selling. I had re-located to a different city but still owned a garage space in the previous residence. I was very unmotivated in renting it out and wanted to get the spot sold. I procrastinated about it for roughly 6 months, kept on paying monthly dues while the spot was empty and not used by any one. The sale seemed a big and complicated step, you could say I was afraid to take it.

One day I sat down to plan the goals for the upcoming year and committed to getting that property sold. I asked myself, what value did the goal of selling the parking garage will serve? Two values clearly stood out:

Financial well being – I would eliminate a monthly maintenance fee and grow my bank account by at least $20k once the sale completed

Clutter free lifestyle – it would be one less thing I owned and had to manage, one less thing to think about

It is important to make the goal fit the value system. Doing so gives you that additional motivation and clarity into why you are doing a task. It comes in handy when going gets tough, when life gets in a way and you start to feel like abandoning the task.

Anyway, depending on where you live and what property you own, selling it is easier said than done. To make it more manageable, I broke it down into more concrete steps. I asked myself, based on my past experience, what do I need to do to get this sold? I need to list the place somewhere where the buyers can see it. How does one do that? Do I know anyone who needs it? No, so the obvious choice is to contact the real estate agent I had worked with in the past. And here we have our first task: get in touch with the real estate agent to list the parking spot. Then I remembered that I will also need a real estate lawyer. Another task: get in touch with the lawyer I had worked with in the past. I sent out the emails to both people, both replied and the ball was rolling. Couple more tasks, exchanges, and events followed. All in all it took 5+ months to sell, but it did sell. Goal accomplished!

There was a point in my life where a goal like that would set me spinning. After all, what do I know about selling things? I would over-think and would tell myself that I will sell this “next year”, or “soon”. Next year would come and I would follow the same approach: over-think the process, over-complicate it really, delay, and procrastinate. Now, when I decide to do something, I try to find the first small actionable step that I can do to get the ball rolling. Take that step, schedule the next step, take it, schedule the next and repeat until the goal is complete.

Depending on how ambitious I want to be, I like to take on 5-8 different goals for a year. Sometimes there are less goals but the goals themselves are larger. That’s arguably a better approach as with fever goals you will be more focused. I still like to have couple things going on at a time as inevitable the progress might stall and I have something else to fall back to. At the end, as long as you are challenging yourself and work on things that are important to you, you will lead a meaningful life and grow as a person.

Through all of this it is important to do a weekly / monthly check-in to evaluate how you are doing with your goals. It is a critical step to make sure you stay on track. During the check-in, I look at the calendar and the recent actions and ask myself:

do the steps I am taking now align with the goals / values?

are the steps getting me closer to accomplishing the goal?

This makes sure that you are not just being busy but actually doing meaningful work that gets you somewhere, that moves you along. Don’t be surprised to see that the action you are taking does not get you any closer. Sometimes you should simply drop it and change up the strategy. If you notice that you are not doing anything, don’t scold yourself nor tell yourself that you “will get better soon” and “get this done”. Those words are empty. Instead try to find the reasons why you are not working on the task. A lot of times I find that the goal or task is still too broad or vague making it hard to start. So I break it down again into something smaller, even more actionable.

I hope this helps someone that is starting to live a life with the plan in mind. I know a process of self-evaluation, dreaming, challenging, and planning helps me lead a richer life, with ups and downs along the way that makes things interesting and at the end of the day very enjoyable.